Bismuth-Catalyzed Intermolecular Hydroamination of 1,3-Dienes with Carbamates, Sulfonamides, and Carboxamides

Hongbo Qin, Noriyuki Yamagiwa, Shigeki Matsunaga,* and Masakatsu Shibasaki*;
Contribution from the Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
J. Am. Chem. Soc., 2006, 128 (5), pp 1611–1614
DOI: 10.1021/ja056112d
Publication Date (Web): January 17, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, smatsuna@mol.f.u-tokyo.ac.jp, ; , mshibasa@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

A Bi(OTf)3/Cu(CH3CN)4PF6 system efficiently promoted intermolecular 1:1 hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides to afford allylic amines in good yield (up to 96%). Reaction proceeded with 0.5−10 mol % catalyst loading at 25−100 °C (generally at 50 °C) in 1,4-dioxane within 24 h. The Bi(OTf)3/Cu(CH3CN)4PF6 system constitutes a new entry into series of intermolecular hydroamination catalysis. Mechanistic studies and the postulated reaction mechanism are also discussed.

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History

  • Published In Issue February 08, 2006
  • Received September 6, 2005

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